Cesium carbonate → tert-butyl (2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate

HRID 624025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624025
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].[C:15]([NH:22][CH2:23][CH2:24]Br)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>CC#N.C(Cl)Cl>[C:18]([O:17][C:15](=[O:16])[NH:22][CH2:23][CH2:24][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Produkt 1

HCID 70984700tert-butyl (2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-nitro-1H-pyrazole (2.50 g, 21.45 mmol) in MeCN (30 mL), Cs2CO3 (8.39 g, 25.74 mmol) and 2-(boc-amino)ethyl bromide (5.45 g, 23.59 mmol) was added. The resulting mixture was refluxed (80° C.) for 1.5 h, then the reaction mixture was allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake was washed with DCM and the filtrate was concentrated in vacuo. The residue was partitionned between water and EtOAc, the org. layer was separated and the aq. layer was extracted with EtOAc (1×). The combined org. layers were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification was performed by FC (EtOAc/hept 7:3 to EtOAc/MeOH 9:1) to obtain tert-butyl(2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate as a slightly yellow solid which was used without further purification in the next step. LC-MS conditions A: tR=0.72 min, [M+H]+=257.08.

Aufarbeitung

  1. customto reach rt
  2. filtrationfiltered
  3. washthe filter cake was washed with DCM
  4. concentrationthe filtrate was concentrated in vacuo
  5. customlayer was separated
  6. extractionthe aq. layer was extracted with EtOAc (1×)
  7. washlayers were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-96e64d8f3fd549dba226c6172b4abc06
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303023B2

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